Guest house holiday rentals in Windsor County

Peace & quiet at Comet Farm

Get your second wind at Comet Farm. Nestled amid rolling hills and sprawling meadows, this retreat sits between Woodstock and Okemo Mountain, a setting for hiking, cycling, skiing, family outings and moments of self-discovery. As the sun bathes the landscape in warm hues, the expanse of big skies will leave you awe-inspired throughout the day, while the night unveils a breathtaking canvas of bright stars. Awaiting you are Vermont experiences such as antique stores, farmers markets and breweries.

Cozy Getaway- Ski, Woodstock, Hanover

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

Moon Acre Farm Green Mountain Oasis - near Okemo

Relax in the mountain stillness, overlooking a pond in a stylish studio guesthouse at Moon Acre Farm. Our guesthouse is off of the main roads, surrounded by 60,000 acres of National Forest, yet 15 miles drive to restaurants, shopping, and boating. The studio is open and spacious (900 sqft), and artistically built into the upper level of our barn to take advantage of the views of the mountains and pond. Enjoy sitting on the balcony overlooking a stream or explore the gardens and woods.

Cozy, clean studio with picturesque Vermont views!

Lovely studio in the heart of the mountains! Our cozy and well-lit space is perfect for solo travelers or couples looking to explore all that Vermont has to offer. Enjoy a queen-sized bed, pull out sofa, kitchenette and a charming bathroom. 2 miles to the Woodstock Village and 1 mile to Saskadena Six (formerly Suicide 6). Experience local life with all the modern amenities you need for a memorable stay. ***In the winter months, 4 wheel drive or all wheel drive is mandatory.***

Cozy Carriage House – Ski Okemo & Magic Mtn

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

Private guesthouse in Lebanon

This cozy one-room guesthouse is located on a quiet street off the green in downtown Lebanon, NH. It offers a private entrance with access to a lovely outdoor patio and gas grill. The room has high ceilings, a full-sized bed, a bathroom/shower, and a kitchenette with coffee maker, electric kettle, microwave, toaster, and compact fridge. A short walk away from restaurants and cafes and a 12-minute drive to Dartmouth College. Please note that there is no kitchen sink or stove.

Macintosh Hill Farm

Originally built in 1817 by the Macintosh Family, our family farm is steeped in historical beauty. Nestled in the hills of Bethel, we live in an area rich with skilled farmers, shepherds, cheese makers, and artists. We make apple cider from our orchard, raise chickens, make maple syrup, and grow produce for our family. Our home is surrounded by far reaching views, big skies and lush countryside. Each booking gets privacy & exclusivity, making our farm your perfect retreat.

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

Brand New Village home in Cavendish, VT

Welcome to Village Home in Cavendish—an inviting Airbnb retreat just 8 minutes away from Okemo Clock Tower Base. Immerse yourself in comfort and style at our brand new 2-bedroom suite, thoughtfully curated for a delightful stay. The apartment, an addition to the main house, spans two levels, providing ample space. Enjoy the convenience of plenty of parking and take advantage of our two 2-level EV charging Outlet. Your comfort is our priority at Village Home

Charming Cavendish Guesthouse w/ Sauna!

Cavendish Cottage Guest House! Freshly renovated with designer touches, this charming guest house blends style, comfort, and Vermont charm. Enjoy free access to our traditional sauna — shared with two other units and your host. Robes robes provided so you can unwind after skiing or hiking, then cozy up by the pellet stove. 10 minutes to Okemo, 2 minutes to groceries, and super comfy vibe await!

Dartmouth Area River House

Charming two-bedroom private apartment in an 1830s farmhouse, right on the Ompompanoosuc River in Norwich, Vermont A ten-minute drive to Dartmouth College and King Arthur Flour. Key Features: Ideal for Dartmouth College alumni, parents, and community members due to its close proximity to the campus. Close to King Arthur Flour and Dartmouth Hitchcock Medical Center.